Composition of matter



ticu. 'l'lusoompoimdisyeryimatable Patented July 31, 1945 COMPOSITION OFMATTER Huh I. McCleary and John 8. Morris, Beacon, N. Y., assignors toThe Texas Company, New York, N. Y., a corporation of Delaware NoDrawins.

Seth! No. 445,962.

'1 Claims.

This invention relates to a metal xanthate of an oil-soluble sulfuriaedphenolic composition derived from the oils extracted from the Anacardiumgenus of the Anacardiaceae family.

- This application is a division of the invention as described andclaimed in the copending application of Bush I". McCleary and John It.Morris, serial No. 445,962, filed June 5, 1942.

The compositions of the present invention are prepared from theextracted oils obtained from the Anacardium genus of the Anacardiaceaefamily and include the compositions andconstituents of such oils ascashew nut shell oil, marking nut shell oil; Japanese lac, etc. It isthe consensus of the authorities on these extracted oils that thechemical compositions. thereof consist primarily of various types ofaromatic derivatives such as Original application June 5, 1942,

Divided and this applidatlon January 6, 1943, Serial No. 471,495

heating forms condensation and polymerization copolymers.

In addition tothe car 1 tained contains a. lower boiling fractionpossessing a nicotine-like odor which rapidly darkens when exposed .tothe atmosphere. This fraction, which anacardic acid (CnHnOa). cardol(CuHs O4),'

cardonal (0:011:20), anacardol (CnHuOland urushiol (cameos).

,The phenolic compositions to which this invention applies are thoseoil-soluble phenols which exist in the naturally occurring -Anacardiumoils or are formed by the decomposition of other aromatic derivativespresent in the oils. These oil-soluble phenols are usually monoordihydric phenols possessing long chain unsaturated allryl groupsattached to the nucleus.

The naturally occurring cashew nut shell oil is described as containingapproximately'90% anacardic acid and cardol. Neither of these -xanthateof an o k 1 c'ardium genus ofthe Anacardiaceae family to a constituentsis applicable to the present invention in that the anacardic acidfraction contains a carboxylic group and the cardol fraction. whiledescribed as a phenolic composition, is relatively oil-insoluble. I

The commercially available cashew nut shell oil which is obtained hy'athermal extraction process consists primarily of a mixture of anacardicacid, cardanol and cards! with cardanol predominating. The cardanoli'raction which does not appear in the naturally occurring oil isresumed to be a degradation product of anacardic acid and the amounts ofcardanol present heat used in the extraction process. Upondistillationof the commercial cashew nut shell oil, an oil-solubledistillate is obtained which consists almost entirely of carda'nol.Carda'nol distiils over as an oil-soluble light-colored liquid atapproximately 225 C. and 10 mm. mercury and is described as a phenolpcssessinganunsaturated alkyl radical of 14 carbon atomjsin' the metaposiin the commercial oil depend upon the degree of,

and upon 5 reactions is not critical to potassium, lithium. calcium.

amounts to about 5% of the original oiLcontains approximately 0.64%nitrogen. If desired, this lower boiling fraction may be removed bytional distillation.

The following physical constants were obtained on two distillates of thecommercially available thermal extracted cashew nut shell 011, one beingobtained by vacuum distillation at 10 mm. mercury (A), and the other bysteam distillation at atmospheric pressure (B):

x l A B s a rs-- ii; iiinzuml i mi fi 6 3. 5 Saponiilcation No. 8.4 Percent sulfur- (l. 10 (i. 10

It has been discovered that the addition of small quantities of anoil-soluble or oil-miscible metal il-soluble sulfurized phenoliccomposition obtained or derived from the Anareilned hydrocarbon 011provides a lubricant, or

a compounding lubricant, possessing enhanced.

anti-oxidant and anti-corrosive properties, to-

gether with lubricating compositions containing small proportions ofthese compounds are described and claimed in the copending applicationof RushF.

McCleary and John R. Morris, Serial No. 445,962, illed June 5, 1942.

The particular metals which may be used to form the metal derivatives ofthe present invention include any of the following metals: sodium.barium, strontium, tin, bismuth, aluminum, zinc, magnesium, mium, lead,titanium, antimony, chromium, manganese, iron, cobalt, nickel andcopper, with preference given to the alkaline earth metals and tin andzinc.

In preparing of the present invention it has been found preferable tothe metal salt thereof and finally reset the metal salt of' thesulfurized phenol with carbon disuliide under-pressure. This particularsequence of fraca lowered pour point. The resulting cadthe sulfuf'ized'metal xanthates first sulfurize theunsaturated c0nstit- 3 uents of thephenolic compositions, then prepare the preparation of these furizationreaction.

compositions and-any of the classical methods of synthesis may be usedwhich will result in the compounds herein described.

In all these reactions particular care must be taken to avoid thepolymerization and condensation reactions characteristic 01' thesephenols, It has been found that by partially hydrogenating theunsaturated alkyl radicals, these undesirable reactions are avoided andthe partially hydrogenated product is sufficiently stable to proceedwith any of the foregoing reactions, These hy- I Example 400 ccs. ofcardanol with abromine number of 104-105 was partially hydrogenated inan Adkins type hydrogenation bomb using' a Raney nickel catalyst under2000 pounds pressure. The resuiting partially hydrogenated cardanolanalyzed as follows:

Bromine No 64-65 Hydroxy1No .a 182-177 Percent sulfur None To 285grams'oi' the partially hydrogenated cardanol were added 315 grams of300 Pale oil and 28 grams of elemental sulfur. The mixture was heatedwith stirring at 150-160 C. for six hours and then cooled. To 314 gramsof the concentrate of the suliurized partially hydroenated cardanol inthe Pale oil were added 50 grams of barium hydroxide and 300 cos. oftoluene. This mixture was refluxed under an auto- 'matic water separatoruntil no more water came off and then cooled, filtered and the solventremoved by stripping.

This product which was a 50% concentrate of barium salt of sulturizedpartially hydrogenated cardanol in Pale oil analyzed as follows:

Percent barium 9.9-10.0 Percent sulfur 8.4

325 grams of the concentrate were charged to a bomb with 325 ccs. ofcarbon disulflde. The bomb was heated to 110-120 C. under a pressure or75 pounds per square inch for 1 /2 hours after which the heat was cutoil and the bomb rocked for seven hours. The contents of the bomb werethen cooled, washed out with carbon disuliide and stripped of solvent.The analysis or the resulting barium xanthate of sulfurized partiallyhydrogenated cardanol in a concentrate of 800 Pale'oil was as follows:

Percent barium 10.0-10.2 Percent sulfur 7.0

hydrogenated phenol obtained from distilled cashew nut shell ofl.

4. 'An alkaline earth metal xanthate of sulfurized partiallyhydrogenated cardanol.

5. A tin xanthateo! sulfurizedpartially hydrogenated cardanol.

6. A metal xanthate of an oil-soluble sulfurized phenol derived from amember of the class consisting of cashew nut shell oil, marking nutshell oil and Japanese lac.

7. A metalxanthate or an oil-soluble sulfurized partially hydrogenatedphenol derived from a member ot the class consisting of cashew nut shelloil, marking nut shell oil and Japanese lac.

RUSH F. McCLEARY. JOHN R. MORRIS.

